Hexachloroethane → 1-Benzyl-2-chloro-7-dimethylamino-5-methyl-1,5-dihydroimidazo[4,5-d]pyridazin-4-one

1.15 ml of a 1 M tetrahydrofuran solution of dibutylmagnesium was added to a 2 ml tetrahydrofuran solution of 0.320 ml of diisopropylamine at room temperature under a nitrogen atmosphere, and the mixture was stirred for 8 hours. This solution was added to a 4 ml tetrahydrofuran solution of 0.162 g of 1-benzyl-7-dimethylamino-5-methyl-1,5-dihydroimidazo[4,5-d]pyridazin-4-one at room temperature under a nitrogen atmosphere, and the mixture was stirred at room temperature for 15 hours. Then, a 5 ml tetrahydrofuran solution of 0.540 g of hexachloroethane was added dropwise to the solution. After the mixture had been stirred for 4 hours, 30 ml of a 5% aqueous ammonium chloride solution was added thereto. The mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed successively with 30 ml of water and 30 ml of a saturated sodium chloride solution, and dried over magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.094 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (2:1).

1. stirringthe mixture was stirred at room temperature for 15 hours
2. stirringAfter the mixture had been stirred for 4 hours
3. extractionThe mixture was extracted with 100 ml of ethyl acetate
4. washThe organic layer was washed successively with 30 ml of water and 30 ml of a saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. concentrationThe organic layer was concentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-1d4b56dbb813449283dfd2950d99f1cf

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772226B2